1,2-dihydroxy-3-<2-(aminoacetyl)-4-<<(tert-butyloxy)carbonyl>oxy>naphthalen-1-yl>propane | 144191-95-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-dihydroxy-3-<2-(aminoacetyl)-4-<<(tert-butyloxy)carbonyl>oxy>naphthalen-1-yl>propane
• 英文别名: [3-Acetamido-4-(2,3-dihydroxypropyl)naphthalen-1-yl] tert-butyl carbonate
• CAS: 144191-95-7
• 化学式: C₂₀H₂₅NO₆
• 分子量: 375.422
• InChiKey: WTJNXKKAAMPTRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-dihydroxy-3-<2-(aminoacetyl)-4-<<(tert-butyloxy)carbonyl>oxy>naphthalen-1-yl>propane 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 53.5h， 生成 (+)-(2R)-3-acetyl-2-<(methylsulfonyl)oxy>-5-hydroxy-1,2,3,4-tetrahydrobenzoquinoline
  参考文献：
  名称：

  Synthesis of CBI-PDE-I-dimer, the benzannelated analog of CC-1065

  摘要：

  A practical synthesis of CBI (2), utilizing inexpensive starting materials, was developed and applied to the synthesis of benzannelated analogs of CC-1065, in particular CBI-PDE-I-dimer (13) and CBI-bis-indole (17). While a Sharpless asymmetric dihydroxylation reaction proved effective at providing optically active intermediates, a more classical resolution procedure was used to prepare materials of higher optical purity. A novel cyclization employing a six-membered-ring intermediate (12) was employed to construct the cyclopropyl ring in CBI. Like CC-1065, CBI-PDE-I-dimer appears to cause delayed toxicity in mice.

  DOI：

  10.1021/jo00049a035
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 四氧化锇 、 甲酸 、 sodium dithionite 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 61.5h， 生成 1,2-dihydroxy-3-<2-(aminoacetyl)-4-<<(tert-butyloxy)carbonyl>oxy>naphthalen-1-yl>propane
  参考文献：
  名称：

  Synthesis of CBI-PDE-I-dimer, the benzannelated analog of CC-1065

  摘要：

  A practical synthesis of CBI (2), utilizing inexpensive starting materials, was developed and applied to the synthesis of benzannelated analogs of CC-1065, in particular CBI-PDE-I-dimer (13) and CBI-bis-indole (17). While a Sharpless asymmetric dihydroxylation reaction proved effective at providing optically active intermediates, a more classical resolution procedure was used to prepare materials of higher optical purity. A novel cyclization employing a six-membered-ring intermediate (12) was employed to construct the cyclopropyl ring in CBI. Like CC-1065, CBI-PDE-I-dimer appears to cause delayed toxicity in mice.

  DOI：

  10.1021/jo00049a035

文献信息

• Synthesis of CBI-PDE-I-dimer, the benzannelated analog of CC-1065
  作者：Paul A. Aristoff、Paul D. Johnson

  DOI：10.1021/jo00049a035

  日期：1992.11

  A practical synthesis of CBI (2), utilizing inexpensive starting materials, was developed and applied to the synthesis of benzannelated analogs of CC-1065, in particular CBI-PDE-I-dimer (13) and CBI-bis-indole (17). While a Sharpless asymmetric dihydroxylation reaction proved effective at providing optically active intermediates, a more classical resolution procedure was used to prepare materials of higher optical purity. A novel cyclization employing a six-membered-ring intermediate (12) was employed to construct the cyclopropyl ring in CBI. Like CC-1065, CBI-PDE-I-dimer appears to cause delayed toxicity in mice.